4733-09-9Relevant academic research and scientific papers
High Activity and Efficient Turnover by a Simple, Self-Assembled "artificial Diels-Alderase"
Martí-Centelles, Vicente,Lawrence, Andrew L.,Lusby, Paul J.
supporting information, p. 2862 - 2868 (2018/03/08)
The Diels-Alder (DA) reaction is a cornerstone of synthesis, yet Nature does not use catalysts for intermolecular [4+2] cycloadditions. Attempts to create artificial "Diels-Alderases" have also met with limited success, plagued by product inhibition. Using a simple Pd2L4 capsule we now show DA catalysis that combines efficient turnover alongside enzyme-like hallmarks. This includes excellent activity (kcat/kuncat > 103), selective transition-state stabilization comparable to the most proficient DA catalytic antibodies, and control over regio- and chemoselectivity that would otherwise be difficult to achieve using small-molecule catalysts. Unlike other catalytic approaches that use synthetic capsules, this method is not defined by entropic effects; instead multiple H-bonding interactions modulate reactivity, reminiscent of enzymatic action.
